About Chastain Real Estate Company

Helping you get the home of your dreams

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I work with you and prioritize your goals. I will be alongside of you every step of the way

My Story

Meet Amy Chastain – the CEO and co-founder of Chastain Real Estate, a company she and her husband, Kevin, started. Amy is committed to putting her clients’ needs first and utilizing her keen negotiating skills to ensure a successful transaction.

Amy understands what it is like to stand in her clients’ shoes. Born and raised in West Lafayette, Indiana, and having to relocate several times – has afforded Amy a sensitivity towards her clients’ journey, which can be attributed to the first-hand perspective she gained through her personal experience.

Amy graduated from Purdue University West Lafayette, IN with a Bachelor’s degree in Organizational Leadership & Supervision. She then took her master’s degree from Lindenwood University St. Charles, MO with a degree in Human Resource Management focused on Training and Development. She joined the Real Estate profession as her five children approached their middle school and high school years.

My Approach

Amy specializes in all facets of the Real Estate business, whether it be navigating the way for the first timers, trying to score that perfect distressed property, or providing help in the luxury market, she knows and has experienced it all.
Amy showcases her homes on her website and utilizes a team of professional; service providers to assist with her clients’ buying and selling needs, including stagers, painters, designers, handymen, and inspectors. She is communicative, thorough, and detail-oriented – and she’ll be alongside you every step of the way.

Meet The Chastain Real Estate Team

Jennifer Staples


Originally from New York, Jennifer moved to the Central Florida area in 2006 to pursue a job with The Walt Disney Company. It was during this time that she honed her world-class customer service and sales skills. This knowledge, coupled with her passion for Real Estate, has provided her with a unique skill set that she uses in every Real Estate negotiation and transaction. After moving a few times around the Central Florida area, Jennifer currently resides in the Winter Garden area with her daughter. She enjoys spending her free time on/in the water, crafting, reading, and traveling. Jennifer proudly volunteers at Give Kids the World Village and supports several great nonprofit organizations.

A Real Estate purchase is one of the most important decisions you will make in your life. Jennifer prefers to work with a limited amount of clients at a time in order to focus on educating homebuyers and sellers, as well as providing a personalized experience.

Jonathan Jankowski


Jonathan is a dedicated agent focused on personalized, dedicated service. With 11 years as a Realtor in the central Florida market, and 17 years providing exceptional Disney service, Jonathan consistently exceeds expectations. No matter the price, Jonathan recognizes the significance of buying, selling or building a home, be it your first or 5th home. He remains engaged through the entire process ensuring all parties are diligently working towards a smooth and successful closing. When not showing homes he spends time with family at the softball fields, downtown winter garden or at the beach.


What the clients are saying

Cindy & Rob Russo

“Amy Chastain has been our REALTOR since 2007 when we purchased a home in Orlando. She couldn’t have made the process easier for us. When we decided to use this property as a rental, we hired Amy as our property manager. (Since we lived in Rhode Island) She again exceeded our expectations. From purchase to rental (including managing several renovations and repairs) to the sale of this home we couldn’t have been happier with her expertise. We consider her part of our extended family.”


Still have some questions? Contact us today and we’ll be in touch soon!